(E)-4-(pyridin-4-yldiazenyl)phenol | 253333-13-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-4-(pyridin-4-yldiazenyl)phenol
• 英文别名: 4-(4-hydroxyphenylazo)pyridine；4-(4-hydroxphenylazo)pyridine；4-(4-pyridylazo)phenol
• CAS: 253333-13-0
• 化学式: C₁₁H₉N₃O
• 分子量: 199.212
• InChiKey: BCBHUOGPSRNKLW-BUHFOSPRSA-N

物化性质

• 熔点：
  265 °C(Solv: methanol (67-56-1); acetone (67-64-1))
• 沸点：
  398.9±22.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.84
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-4-(pyridin-4-yldiazenyl)phenol 在 氢氧化钾 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-[4-(4-pyridylazo)phenoxy]undecanoic acid
  参考文献：
  名称：

  Self-Assembly of Amphoteric Azopyridine Carboxylic Acids:  Organized Structures and Macroscopic Organized Morphology Influenced by Heat, pH Change, and Light

  摘要：

  In this paper, we describe the synthesis of novel amphoteric azopyridine carboxylic acids (2b, 3a, 3b, 4a, and 4b), having both a carboxyl group as a hydrogen donor and a pyridyl group as an acceptor at each molecular terminus, and their self-organization, which is markedly affected by external stimuli including heat, pH changes, and light. The amphoteric compounds form intermolecular hydrogen bonds between pyridyl and carboxyl groups in a head-to-tail manner in the solid state to give linear pseudopolymer structures, as supported by FT-IR analysis. Heating and cooling across their melting points induced thermoreversible supramolecular depolymerization to and polymerization from small molecular components of monomers and the corresponding carboxylic acid dimers. In alkaline aqueous media, these amphoteric compounds, dissolved as carboxylate anions, were gradually neutralized by atmospheric carbon dioxide, leading to their deposition as novel fibrous materials from 3b and 4b, substituted with a propyl group at the phenyl ring, and as leaflet crystals from 3a and 4a bearing no substituent. FT-IR and X-ray diffraction measurements supported the conclusion that the formation of fibrous materials from 3b and 4b arises from their intermolecular hydrogen bonding in a head-to-tail manner as well as the suppressive effect of propyl substitution on the pi-pi stacking of the molecules. UV irradiation of alkaline solutions of 4b resulted in the modification of the morphology of fibrous materials, probably because the photoisomerized Z-isomer of 4b affected the nucleation process in the fibrous formation. These results suggest that morphological properties of these macroscopic self-assemblages are tunable by appropriate choices of environmental stimuli such as heat, pH, and light.

  DOI：

  10.1021/ja001790f
• 作为产物：
  描述：

  4-(pyridin-4-ylhydrazinylidene)cyclohexa-2,5-dien-1-one 以 乙醇 为溶剂， 生成 (E)-4-(pyridin-4-yldiazenyl)phenol
  参考文献：
  名称：

  Photo-driven optical oscillators in the kHz range based on push–pull hydroxyazopyridines

  摘要：

  推拉偶氮苯酚是稳定光驱动光振荡器的重要目标分子。羟基氮吡啶甲基碘盐的振荡频率高达 10 kHz，连续工作时不会出现疲劳迹象。

  DOI：

  10.1039/c1cc10302d

文献信息

• Tuning the photonic properties of chiral nematic mesoporous organosilica with hydrogen-bonded liquid-crystalline assemblies
  作者：Michael Giese、Tim Krappitz、Ronald Y. Dong、Carl A. Michal、Wadood Y. Hamad、Brian O. Patrick、Mark J. MacLachlan

  DOI：10.1039/c4tc02602k

  日期：——

  The thermochromic behaviour of chiral nematic mesoporous organosilica hybrids infiltrated with hydrogen-bonded liquid crystals was investigated by polarized optical microscopy, UV-vis and CD-spectroscopy.

  手性向列介孔有机硅杂化材料与氢键液晶的热致变色行为通过偏振光学显微镜、紫外可见光谱和圆二色光谱进行了研究。
• Hydrogen bonding interactions affect the hierarchical self-assembly and secondary structures of comb-like polypeptide supramolecular complexes displaying photoresponsive behavior
  作者：Mohamed Gamal Mohamed、Jia-Huei Tu、Shih-Hung Huang、Yeo-Wan Chiang、Shiao-Wei Kuo

  DOI：10.1039/c6ra07907e

  日期：——

  this study we blended 4-(4-hexadecylphenylazo)pyridine (AzoPy-C16), synthesized through facile diazonium and monoetherification reactions, with polytyrosine (PTyr) to form comb-like polypeptide supramolecular complexes stabilized through hydrogen bonding between the pyridyl...

  在这项研究中，我们将通过简单的重氮和单醚化反应合成的4-（4-十六烷基苯基偶氮）吡啶（AzoPy-C16）与聚酪氨酸（PTyr）混合形成梳状多肽超分子复合物，该复合物通过吡啶基之间的氢键稳定化。
• Is chemical crosslinking necessary for the photoinduced bending of polymer films?
  作者：Jun-ichi Mamiya、Akira Yoshitake、Mizuho Kondo、Yanlei Yu、Tomiki Ikeda

  DOI：10.1039/b715855f

  日期：——

  Freestanding crosslinked liquid-crystalline polymer films obtained by self-assembly through intermolecular hydrogen bonding showed photoinduced bending and unbending. The structural change at the microscopic level, caused by trans–cisphotoisomerization of the azobenzene moieties at the hydrogen-bonded crosslinks, is successfully converted into a macroscopic deformation in the liquid-crystalline polymer films.

  通过分子间氢键自组装获得的独立交联液晶聚合物薄膜显示出光诱导的弯曲和不弯曲。偶氮苯分子在氢键交联处的反式异构化引起的微观结构变化成功地转化为液晶聚合物薄膜的宏观变形。
• Azo Dyes Functionalized with Alkoxysilyl Ethers as Chemodosimeters for the Chromogenic Detection of the Fluoride Anion
  作者：Alessandro Agostini、Michele Milani、Ramón Martínez-Máñez、Maurizio Licchelli、Juan Soto、Félix Sancenón

  DOI：10.1002/asia.201200323

  日期：2012.9

  Finding fluoride: An azo dye functionalized with tert‐butyldimethylsilyl ether has been synthesized and used as a selective chromogenic fluoride sensor in the acetonitrile/water mixtures. The chromogenic response arises from the fluoride‐induced hydrolysis of the silyl ether moiety, which yields a highly colored phenolate anion. The sensor molecule can be grafted to silica to make dip‐sticks for fluoride

  寻找氟化物：已经合成了用叔丁基二甲基甲硅烷基醚官能化的偶氮染料，并将其用作乙腈/水混合物中的选择性发色氟化物传感器。发色反应是由氟化物诱导的甲硅烷基醚部分水解而产生的，生成高度着色的酚盐阴离子。传感器分子可以接枝到硅胶上，制成用于氟化物感测的量油尺。
• Mechanism of the benzidine disproportionation of (arylhydrazo)pyridines. The reactions of 4-(4-chlorophenylazo)pyridine and -hydrazo)pyridine in acid media
  作者：Robin A Cox、Kap-Soo Cheon、Sam-Rok Keum、Erwin Buncel

  DOI：10.1139/v98-082

  日期：1998.6.1

  A kinetic and product analysis study of the reactions of 4-(4-chlorophenylhydrazo)pyridine (1) and 4-(4-chlorophenylazo)pyridine (2) in acid media is reported. The disproportionation of two moles of 1 in aqueous sulfuric acid gives one mole of the oxidized product 2, and one mole each of the reduced products 4-chloroaniline and 4-aminopyridine. The azo compound 2, a product of the reaction of 1, undergoes

  报道了 4-(4-氯苯偶氮) 吡啶 (1) 和 4-(4-氯苯偶氮) 吡啶 (2) 在酸性介质中反应的动力学和产物分析研究。2 摩尔的 1 在硫酸水溶液中歧化得到 1 摩尔的氧化产物 2 和各 1 摩尔的还原产物 4-氯苯胺和 4-氨基吡啶。偶氮化合物 2 是 1 反应的产物，在酸性介质中进行较慢的羟基化反应，并且还研究了该过程。2 反应中的第一个产物可能是 4-（4-羟基苯基偶氮）吡啶，4-氯被取代。在用于动力学测量的低底物浓度下，两种反应都很简单，但在用于产物分离研究的高得多的浓度下，会产生复杂的产物混合物，其中一种产物是二聚体。由于稳定性的原因，必须使用1作为其盐酸盐，从而增加了复杂性，并且氯离子还可以与浸...